HCID 57467616, compound → Methyl 3-(2,2-dimethylcyclopentyl)-4-hydroxybenzoate

HRID 1662377Notes

Reaction equation

HRID 1662377 reaction equation
C([O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=1[C:19]1[C:23]([CH3:25])([CH3:24])[CH2:22][CH2:21][CH:20]=1)C1C=CC=CC=1>CO.[Pd]>[CH3:24][C:23]1([CH3:25])[CH2:22][CH2:21][CH2:20][CH:19]1[C:10]1[CH:11]=[C:12]([CH:17]=[CH:18][C:9]=1[OH:8])[C:13]([O:15][CH3:16])=[O:14]

Participants

4

Reactant 1

HCID 57467616HCID 57467616, compound

Product 1

HCID 57467593Methyl 3-(2,2-dimethylcyclopentyl)-4-hydroxybenzoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a flask containing 66.11D (3.03 g, 9.0 mmol) in MeOH (25.0 mL) was added palladium, 10% wt. on activated carbon (0.48 g, 0.45 mmol). After purging, the mixture was stirred under an atmosphere of hydrogen at room temperature. The reaction was monitored with TLC and LC-MS. After 27.5 hours, the reaction was filtered through Celite. After concentration, the residue was purified on silica gel using 0-50% EtOAc in hexanes to yield 66.11E as a colorless oil that solidified (1.99 g, 89%). 1H NMR (400 MHz, CDCl3) δ ppm 7.91 (1H, d, J=2.3 Hz), 7.79 (1H, dd, J=8.4, 2.2 Hz), 6.82 (1H, d, J=8.2 Hz), 5.54 (1H, s), 3.90 (3H, s), 3.17 (1H, dd, J=10.4, 8.0 Hz), 2.17 (1H, m), 2.04 (1H, m), 1.92 (1H, m), 1.81 (1H, m), 1.68 (2H, m), 1.06 (3H, s), 0.72 (3H, s).

Workup

  1. customAfter purging
  2. filtrationthe reaction was filtered through Celite
  3. concentrationAfter concentration
  4. customthe residue was purified on silica gel using 0-50% EtOAc in hexanes

Sources & evidence

ORD record
ord-0f790bbedd5d403baa9f236760f97138
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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